“Fading Gigolo” isn’t about fulfillment, sexual or otherwise — it’s about the transitions in the lives of its characters.

Fading Gigolo, written and directed by John Turturro. At Kendall Square Cinema and other Boston area theaters.

John Turturro and Sofía Vergara in “Fading Gigolo.”

By Betsy Sherman

Fading Gigolo is like a box of chocolates: from one scene to the next, you don’t know what you’re gonna get. For his fifth feature as a writer-director, John Turturro casts himself as an unmoored middle-aged New Yorker convinced by a crackpot friend to offer sexual services to women in exchange for money. The premise is played both for comedy and for poignant drama. But the integration of these two aspects just doesn’t come off, which leaves the film only kind of funny, kind of touching.

A tone of nostalgia is set in the film’s opening frames, with shaky home-movie-like footage accompanied by the whir of a living-room projector. Fioravante (Turturro) and Murray (Woody Allen, hewing closely to his comic persona) are packing up the contents of a rare book shop that has been in Murray’s family for generations, but is now closing. Murray, looking for a hustle, says his female dermatologist asked him if he knew someone with whom she and a girlfriend could have ménage à trois. It’ll cost a thousand, Murray told her. Murray was thinking of Fioravante, and of himself getting a cut. The unattached, underemployed younger man says all right.

Don’t expect a well-thought-out consideration of masculine prostitution on the order of the HBO show Hung. The gigolo part of Fading Gigolo is the least satisfying aspect of the movie. And I’m not saying that because of the star’s off-kilter looks (whether intentional or not, the movie is an ode to the triumph of odd-looking guys in middle age, or what I call the how did Ringo get better looking than Paul? phenomenon). Murray’s dubious powers of persuasion get Fioravante in with the tandem of Sharon Stone, no less, as the unhappily married and distractingly glamorous dermatologist, and Sofía Vergara as her frisky friend (their glorified-cameo roles are grating rather than hilarious). But how they extend to making a further bevy of clients part with wads of cash for the services of the dour man-toy is preposterous. It is fun, though, to watch Murray celebrate with a spending spree.

And what about our fifty-something hero? The poker-faced Fioravante doesn’t say much about himself in our presence. He has a blue-collar feel to him and works part-time in a flower shop, making Japanese-influenced arrangements. There’s no mention of his ever being married. He lives alone and has good taste in literature. Neither the word gigolo (“ho” is the preferred quip) nor the song it’s associated with figure into the movie, but the sentiment of these lyrics forms an undertone:

There will come a day
Youth will pass away
Then what will they say about me?

Ultimately, the gigolo stuff builds a bridge so that Fioravante can meet a woman with whom he wouldn’t have otherwise crossed paths. Their relationship is the creamy romantic center of the movie. Avigal (Vanessa Paradis in a warm performance) is introduced as The Lice Lady. Murray lives with a black woman (friend rather than girlfriend, I think), to whose kids he’s “Papa Moe.” When one needs his hair treated for lice, it’s off to Chasidic Williamsburg, Brooklyn, and the apartment of Avigal, the forty-ish widow of a rabbi. It takes yet another suspension of our disbelief to accept that Murray cajoles her to visit a “healer” he knows in Manhattan. In that familiar stammer, he assures her the man is, er, Jewish, er, Sephardic.

Fioravante plays massage therapist for this encounter. Contact between his hand and her bare back is, according to the strict patriarchal code under which she lives, a transgressive “breach of modesty.” In the moment, it’s earth-shatteringly emotional. The pair talk about how hard loneliness can be, but also agree in the resonance of the quotation “Where there is love, there is pain.” These sentiments would be shared by the man following them, if he were as poetically minded as Fioravante. But Dovi (Liev Schreiber), a member of the Williamsburg Shomrim Safety Patrol, considers himself a man of action — except when it comes to declaring his love for Avigal. He instigates a cross-cultural showdown — among Jews, that is — when he and the patrol abduct the secular Murray and haul him in front of a rabbi’s council. Bob Balaban, a lawyer pal who comes to Murray’s rescue, joins Allen and Schreiber as the movie’s comedic sharpshooters.

On the serious side — where Turturro the actor firmly places himself — Fading Gigolo isn’t about fulfillment, it’s about the transitions in the lives of its characters. Cinematic links are made among graying sideburns, autumn leaves, decaying edifices and the grown-up pleasure of a jazz score. Sadly, the film is a leaky vessel. Turturro, one of the finest screen actors of his generation, still struggles (after his promising debut, Mac) to transition into a credible filmmaker.

Betsy Sherman has written about movies, old and new, for The Boston Globe, The Boston Phoenix, and The Improper Bostonian, among others. She holds a degree in Archives Management from Simmons Graduate School of Library and Information Science. When she grows up, she wants to be Barbara Stanwyck.